Dimethylformamide → N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

HRID 1368611Notes

Reaction equation

HRID 1368611 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:30][CH2:31][CH2:32][OH:33])=[N:14][N:15]([CH3:29])[C:16]=3[NH:17][S:18](/[CH:21]=[CH:22]/C3C=CC=CC=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1.[Cl:34][C:35]1[CH:36]=[N:37][C:38](S(C)(=O)=O)=[N:39][CH:40]=1.[Cl-].[NH4+:46].[CH3:47][N:48]([CH3:51])C=O>O>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]3[C:13]([O:30][CH2:31][CH2:32][O:33][C:38]4[N:37]=[CH:36][C:35]([Cl:34])=[CH:40][N:39]=4)=[N:14][N:15]([CH3:29])[C:16]=3[NH:17][S:18]([C:21]3[N:46]=[CH:47][N:48]([CH3:51])[CH:22]=3)(=[O:20])=[O:19])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27277255-Chloro-2-methanesulfonylpyrimidineHCID 22281926HCID 22281926, compound

Product 1

HCID 9871777N-(4-(1,3-benzodioxol-5-yl)-3-{2-[(5-chloro-2-pyrimidinyl)oxy]ethoxy}-1-methyl-1H-pyrazol-5-yl)-1-methyl-1H-imidazole-4-sulfonamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil, 20 mg) was carefully added to a solution of (E)-N-[-4-(1,3-benzodioxol-5-yl)-3-(2-hydroxyethoxy)-1-methyl-1H-pyrazol-5-yl]-2-phenyl-1-ethenesulfonamide (Preparation 44) (100 mg) in anhydrous dimethylformamide (4.4 ml) at room temperature under an atmosphere of nitrogen. After 10 minutes the 5-chloro-2-(methylsulfonyl)pyrimidine (104 mg) was added and the mixture was stirred overnight. To the reaction mixture was then sequentially added an aqueous solution of ammonium chloride (4 ml) and water (30 ml) before being extracted with ether (3×8 ml). Combined organic phases were sequentially washed with water (20 ml), brine (20 ml), dried over magnesium sulfate and concentrated under reduced pressure. A purification by column chromatography (silica, 10 g) eluted with dichloromethane:methanol (95:5) yielded the title compound as a colourless oil (85 mg).

Workup

  1. extractionbefore being extracted with ether (3×8 ml)
  2. washCombined organic phases were sequentially washed with water (20 ml), brine (20 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customA purification by column chromatography (silica, 10 g)
  6. washeluted with dichloromethane:methanol (95:5)

Sources & evidence

ORD record
ord-280b53883d0248358a76d0376ec1c856
Source dataset
uspto-grants-2003_06
Patent number
US06573270B1

Reaction notes

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